The Portugese boss has scraped by with a net spend of zero after pursuits for Joao Moutinho and Leandro Damiao both faltered on the final day of the last two transfer windows

SPECIAL REPORTBy Duncan Castles

There was a sense of inevitability as Emmanuel Adebayor hurried forward to scoop his penalty kick over the crossbar at St Jakob-Park. Sometimes unplayable, more often unreliable, Tottenham Hotspur's best paid footballer had suffered a night of consistently pursuing the wrong option. Ultimately it handed Andre Villas-Boas his first Europa League exit.

Just missing out on his second semi-final was an accident manufactured many months before. Villas-Boas identified Tottenham's need for an elite centre forward before accepting the manager's position last summer, yet his new employers' quixotic approach to transfers saw the club start the new season with a weaker attack than they ended the old one.

THE ONES THAT GOT AWAY

LEANDRO DAMIAO

Internacional, who lost Oscar to Chelsea last summer, were in no mood to sell their striker despite it being the off-season.

JOAO MOUTINHO

The Portugal midfielder had shone at Euro 2012 throughout June, but Spurs left it until August 31 to get their man.

His White Hart Lane wages effectively subsidised by a vast pay-off from Manchester City, Adebayor signed permanent terms on August 21. For all Jermain Defoe's improvement under Villas-Boas' tutelage, by winter it was clear that the club needed a striker with the physique to play up front alone and the capacity to score consistently.

The Portuguese was clear that this man was Leandro Damiao, a Brazil international who Tottenham had independently pursued for well over a year. The majority of the January window was spent waiting for Daniel Levy to be convinced of the value of investing heavily in the 23-year-old. On deadline day Internacional agreed to sell for £15.7 million. Then changed their mind.

With no time left to renegotiate and Levy piqued by such Brazilian brinkmanship, Villas-Boas was left to battle on with an unimproved squad. His situation was all the more frustrating for its familiarity – an almost carbon copy of Tottenham's failure to seal the deal for Joao Moutinho exactly five months before.

Like Damiao, Moutinho had been the manager's absolute priority. Like Damiao's, the transfer promised be an expensive, complex affair because Moutinho's club had no desire to lose him. And like Internacional, Porto's response to Levy's deadline-day negotiating was to first settle on a fee (of £22m plus £2.5m in variables), then increase their asking price as the clock ran down. When Tottenham met even that, some errant paperwork ensured the deal did not go through.

Though time-pressured bargaining has served Levy well in the past and appeals to the chairman's combative nature, it works better when the numbers are lower or he is seller rather shopper. Porto's elevated position in European football has been built upon their transfer market acumen and negotiations for individuals of Moutinho's quality can be too complex to be concertinaed into a single day.

The result of those two deadline-day failures is that Villas-Boas' debut season has been run on a zero net spend. This year's Tottenham are fitter, better prepared tactically and more maturely man managed than the squad Harry Redknapp fronted. With six matches to play they remain in position to qualify for the Champions League, combining an impressive domestic campaign with a serious tilt at the Europa League. Listen to Redknapp and you'd have thought such a strategy both impossible and worthless.

What happens next will be telling. Though he constantly researches options to strengthen his personnel, Villas-Boas has no set budget for next season. With Tottenham still seeking to finance White Hart Lane's rebuild, their manager expects his transfer spend to be determined by the presence (or not) of Champions League football and the club's success in securing a new shirt sponsor. The value of the commercial deal could be tied to the European competition Tottenham end up playing in.

Wherever they are Villas-Boas wants to retain Gareth Bale. The Welshman's agents have other ideas and have been preparing the ground for a move elsewhere – most keenly to Real Madrid – since long before Tottenham's change of management. Having improved Bale's game this season, Villas-Boas is excited by what could be achieved together in the Champions League. And he is also unconvinced that full revenues from a sale would be available for reinvestment.

Villas-Boas will once again pursue a striker (Aston Villa's Christian Benteke has been offered to the club but is far from being first choice). He believes the team would benefit from a playmaker in the mould of Willian, who was eager to work with him at Tottenham before Anzhi Makhachkala threw manic money at Shakhtar Donetsk for the Brazilian's January signature. His scouts have been looking at left-backs and a cadre of top-tier teenagers.

If Tottenham have learned their lesson they will not reach the sharp end of next season relying on a single, infamously flaky centre forward.